Fluorenone, hydroxylation

Table III summarizes some information on the initial rates of oxidation of fluorene in several solvents. In the alcohol-containing solvents the stoichiometry was nearly one molecule of oxygen per mole of fluorene, an observation that excludes 9-fluorenol as an intermediate. In all solvents, including HMPA, interrupted oxidations yielded only fluorenone (or the DMSO-fluorenone adduct) and fluorene. Apparently Reaction 6 or 7 occurs readily in the presence of hydroxylic solvents. In HMPA the high...

Experiments with deuterated optically active primary amyl alcohol, fluorenone, and sodium ethoxide, for example, showed a direct transfer of hydrogen from the hydroxyl carbon to the carbonyl carbon atom without intervention of the solvent.41 We should expect that, like all carbonyl additions, hydride addition reactions would be acid-catalyzed. Apparently, in aluminum isopropoxide and isopropyl alcohol the optimum acid strength of the solution has been reached. Some alkoxide ions... 

ATF was prepared by the reaction route shown below. p-Fluoro-phenyl acetylene (6.00 g) was added to 9,9-bis(4-hydroxyphenyl) fluorenone (8.50 g) in dimethylsulfoxlde (230 ml) containing 25.8 g of potassium carbonate. The reaction was carried out under an inert atmosphere at 130°C for 4 days. The progress of the reaction was followed by monitoring disappearance of hydroxyl band at 3400 cm and appearance of acetylene band at 3300 cm . The reaction mass was then mixed with aqueous potassium hydroxide to remove... 

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